CATALOGUECOURSESOffSec Experienced Penetration Tester (OSEP)
    Cyber Security Certification
    [ cyber ]
    BODY: OffSec

    "The OffSec Experienced Penetration Tester, or OSEP, is a premier certification designed for advanced cybersecurity professionals. It teaches the critical skills necessary to bypass modern security defenses, including Antivirus and Endpoint Detection and Response systems. Security Career Navigator recommends this course for red teamers and penetration testers seeking to master advanced Active Directory exploitation, payload obfuscation, and covert post-exploitation techniques in hardened enterprise networks."

    The OffSec Experienced Penetration Tester (OSEP) course, officially designated as PEN-300, is an advanced, professional-level offensive security certification program designed for seasoned penetration testers. It focuses heavily on evasion techniques, bypassing endpoint security controls (AV/EDR), advanced Active Directory exploitation, and post-exploitation persistence methodologies. The comprehensive curriculum equips intelligence-grade red teamers and offensive security professionals with the procedural standards required to breach mature, hardened enterprise environments, evade detection, and maintain covert access. Graduates of this course are prepared to conduct highly sophisticated threat simulations and adversarial emulation operations.

    Certifying BodyOffSecAccreditation Authority
    Estimated Time85 HoursRecommended Preparation
    Skills Tested5 CompetenciesAtomic Units Mapped
    SecNav Verification
    Active Audit Node
    Simulation Ready

    [01] Hands-On Verification Sandboxes (Live Simulations)

    Deploy into hands-on sandbox simulations mapped directly to OffSec Experienced Penetration Tester (OSEP) objectives. Verify your readiness under real-world conditions:

    Verification Available

    Operation Helix Frost: Insider Threat Simulation

    ID: SECM-4940Deploy
    Verification Available

    APT Containment: Logistics Pivot

    ID: SECM-9832Deploy
    Verification Available

    Operation Cipher Burn: Assumed Breach Containment

    ID: SECM-1439Deploy

    [ EDITORIAL_INDEPENDENCE_NOTICE ]

    SecNav is not a commercial partner for this course. We do not receive compensation, referral commissions, or affiliate fees from OffSec for indexing this credential. We map this path purely for its educational merit and alignment with career progression.

    PROVIDER_INTEL

    [02] Exam Curriculum & Syllabus Modules

    5 Modules Indexed

    Structured domain syllabus and core learning outcomes covered in the OffSec Experienced Penetration Tester (OSEP) examination blueprint:

    MODULE // 01
    ~15h

    Module 1: Advanced Payload Creation & Obfuscation

    • •Client-Side Code Execution with Office
    • •Client-Side Code Execution with Jscript
    • •C# and PowerShell Tradecraft
    • •Shellcode Generation and Obfuscation
    MODULE // 02
    ~20h

    Module 2: Antivirus & EDR Evasion Tactics

    • •Bypassing Antivirus Signatures
    • •In-Memory Injection Techniques
    • •Unmanaged PowerShell and AMSI Bypass
    • •API Hooking Evasion and Process Hollowing
    MODULE // 03
    ~25h

    Module 3: Advanced Active Directory Exploitation

    • •Kerberos Delegation Attacks
    • •Active Directory Trust Boundary Bypass
    • •MSSQL Database Exploitation and Lateral Movement
    • •NTLM Relay and Coercion
    MODULE // 04
    ~10h

    Module 4: Kiosk Breakouts & Application Whitelisting

    • •Restricted Environment Escapes
    • •Windows Defender Application Control (WDAC) Bypass
    • •AppLocker Evasion Techniques
    MODULE // 05
    ~15h

    Module 5: Network Filters & Covert Persistence

    • •DNS, ICMP, and SSH Tunneling
    • •Reverse Proxies and Port Forwarding
    • •Custom C2 Infrastructure Deployment
    • •Advanced Post-Exploitation Persistence Mechanisms

    [03] Skills Validated by This Certification

    The OffSec Experienced Penetration Tester (OSEP) curriculum tests and measures critical capabilities across these essential cybersecurity & threat defense skills. Explore the dedicated skills nodes below:

    Evasion Techniques (AV/EDR)

    cyber

    Active Directory Exploitation

    cyber

    Payload Obfuscation (Shellcode)

    cyber

    PowerShell for Security (Offense)

    cyber

    Post-Exploitation Persistence

    cyber

    [04] Career Pathways & Target Roles

    Securing a verified status in OffSec Experienced Penetration Tester (OSEP) is a high-value accelerator for major cyber defense career paths. Learn more about the primary roles mapping to this pathway:

    Red Team Operator

    Verified Target Role

    Red Team Lead

    Verified Target Role

    Endpoint Security Engineer

    Verified Target Role

    Malware Analyst

    Verified Target Role

    Exploit Developer / Researcher

    Verified Target Role

    Network Penetration Tester

    Verified Target Role

    Junior Penetration Tester

    Verified Target Role

    Cloud Penetration Tester

    Verified Target Role

    Security Researcher (Software)

    Verified Target Role

    [05] Frequently Asked Questions about OffSec Experienced Penetration Tester (OSEP)

    Yes, absolutely! You can verify your real-world readiness by launching the following active-threat sandbox simulations on our platform: Operation Helix Frost: Insider Threat Simulation, APT Containment: Logistics Pivot, Operation Cipher Burn: Assumed Breach Containment. Completing these sandboxes grants cryptographically signed proof and reward XP.
    Students should possess a solid understanding of penetration testing methodologies, typically equivalent to the OSCP (OffSec Certified Professional) certification, along with working knowledge of Python, C#, and PowerShell scripting for offensive operations.
    Yes, a core component of the PEN-300 curriculum focuses on payload obfuscation, memory injection, and bypassing modern Antivirus and Endpoint Detection and Response (EDR) solutions using custom development and advanced evasion tactics.
    The OSEP exam is a grueling 48-hour practical, hands-on assessment where candidates must compromise a simulated enterprise network, bypass defenses, and achieve specific objectives, followed by a 24-hour documentation and reporting period.

    [06] Authoritative Sources & Certification References

    Certifying Body & Official Resources

    Official Registration URLDirect Link
    https://www.offsec.com/courses/pen-300/
    MITRE ATT&CK ReferenceTA0005
    Official Link
    NIST NICE Framework ReferencePR-PTA-001
    Official Link